


Jack of all trades

by UnknownRegion



Category: Undertale (Video Game)
Genre: "Jack" Remembers Resets, Alternate Universe - Soulmates, Angst with a Happy Ending, Groundhog Day, Like dead babies and orphans, M/M, Morally Flexible, OC has a loose moral compass, Other Ships Not Mentioned in Tags, Post-Undertale Pacifist Route, References to Undertale Genocide Route, Sans Has Issues, Sans Remembers Resets, Time Loop, You Have Been Warned, dark humour
Language: English
Status: In-Progress
Published: 2018-03-12
Updated: 2018-03-30
Packaged: 2019-03-29 20:20:09
Rating: Mature
Warnings: Graphic Depictions Of Violence, Major Character Death, Underage
Chapters: 2
Words: 6,982
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13934628
Author URL: https://archiveofourown.org/users/UnknownRegion/pseuds/UnknownRegion
Summary: When someone is born, they are Markless because they lack half a Soul - the missing piece having attached itself to their Soulmate. As they grow older, however, one of their eye colours will gradually change to match their partner's. Researchers believed that this phenomenon is caused by the other half of their Soulmate's Soul slowly stitching itself to form a complete one.Sans has always been conscious of his Mark. And if a skeleton with a floating eyeball wasn't freaky enough, his Soulmate's Soul was inverted as well.





	1. All alone... or not?

**Author's Note:**

  * For [GenderlessPerson](https://archiveofourown.org/users/GenderlessPerson/gifts).



> Shite... I wasn't actually planning on writing or even posting this. 
> 
> I was simply WhatsApp-ing a friend, and suddenly, this soulmate AU idea just hit me in the face. My friend soon persuaded me to write this down as an idea for my next work or something (queue number 20, actually), and I complied. 
> 
> ... Half an hour later and the idea blossomed into a backstory for the characters and plot ┐(´д`)┌  
> Hell, I didn't even notice that I had drawn the eyes as well (ㆆᴗㆆ;)  
> ...  
> ..  
> .  
> orz
> 
> P.S. I do not own Undertale, obviously. Toby Fox is the genius behind this awesome game.

Chester has a love-hate relationship with his bed. Nothing wrong with it. It was all on him, not the bed. In fact, it's super comfortable and warm. It's just that... well, it has been years(?) since he voluntarily went to sleep in his bed. Usually, he would simply  ~~bleed out~~  pass out on the sofa.

With a small yawn, he pushed himself up to check the date.

_October 1_

Another fresh loop has begun, huh?

He shakes his head with a forlorn sigh, having already expected the world to 'stutter' as soon as Halloween ended. The cycle was unpredictable, sure, since it could've lasted an hour, a day, a week, or even a month. But he has never made it to the two-month mark before. 

October the first... The day the Monsters would surface.

Just as he thought of that, a news anchor on TV (he never bothered to turn it off) announced to the world that thousands of intelligent, 'new' species have appeared from Mount Ebott. 

He didn't bother to listen further, knowing how it would all play out. Without much fuss, he got ready for the day, making sure to dress in comfortable clothing such as a baggy black hoodie and space fade joggers, followed by a pair of fluffy blue slippers that people would **only** wear indoors.

As soon as he was ready, he pocketed his phone and wallet and walked out of his mansion.

People often wondered how a young man like him was able to afford such an expensive place... but what they didn't know was that he had been an underground cage fighter since he was a teenager. The dough was great, and he was somewhat unbeatable. Especially after the loop began. His fighting skills only got better with each 'Reset' he lived through. 

When he stepped into his garage, he ignored the half-finished missile situated directly at the middle and jumped onto his favourite bike - a chopper. 

There were a lot of things he turned a blind eye to in this garage. Mainly weapons of mass destructions and other deadly things he shall not name. They were all custom made by yours truly, too. 

After years (maybe...? he lost count, actually) of living the same day (or week/month) over and over again... He dabbled in a lot of things to keep his mind from deteriorating. Doing everything repeatedly was a sign of insanity, so he would try lockpicking one cycle, and eating chocolate from all over the world at the next. It depended mostly on his mood and cravings.

Now... He just wanted to have breakfast at his favourite cafe.

Whilst he rode at maximum speed without a single care, he thought back to how his 'journey' had been.

The start date hadn't always been October the 1st.

It used to be September the 15th.

As soon as the Monsters surfaced, however, the date changed. It was as if the one responsible for all of his misery and happiness during those loops had decided to put a 'save point' (sue him for being a gamer) after the Monsters' appearance.

Within that half a month period, he had built many ~~explosives~~  things and stored them in his garage for later... but because of this latest development, he was unsure if he should continue with his plans of playing terrorism. He, of course, after a few cycles of weighing the pros and cons, decided against it. What if he somehow got caught and the dude refused to 'reset'? He would be fucked for life with a criminal record (or executed). 

So for now, he stuck to only one illegal dealing - which was his usual underground fights. The rest of the time he spent doing new things like learning about other languages, or how to hack through military-grade firewalls, or even playing surgeon. Hell, his current hobbies were Japanese flower arrangements and tea ceremonies just because.

Sometimes, he felt that he dabbled too much.

"Welcome!"

A waiter's cheerfully greeting brought him out of his thoughts.

Wow. He didn't even notice that he had parked his 'gangsta' bike and entered the cafe.

Whilst he sat at his regular table next to the window, he inhaled deeply, the aroma of roast coffee beans giving him a peace of mind.

Without having placed an order, the waiter has already brought him a cup of doppio along with two honey layered scones.

"Thanks, Steve." 

~~_"No worries, mate."_~~

"No worries, mate.

"How's life been treating you?"

~~_"Ah, girl troubles, I'm afraid. Best I not ruin your morning with that."_ ~~

"Ah, girl troubles, I'm afraid. Best I not ruin your morning with that."

"Sarah, again?"

~~_"The usual. I bet she's on her... you know."_ ~~

"The usual. I bet she's on her... you know."

The waiter flushed red from embarrassment and hurriedly excused himself when another customer called. 

Having expected that, he had already turned back to his breakfast, an empty smile playing on his lips.

Just another scripted day. 

As he sipped his espresso, his eyes roamed the cafe.

He knew all of the customers and staff here, having conversed with them until he has a tight grasp on their deepest and darkest secrets. Back then, he had this  **phase**  where his curiosity of humanity was never-ending, so he used different scenarios to... learn about them. He would walk around town and just... assimilate.

Their **expressions.**

> _A woman in a green dress was smiling up at him, her eyes filled with love as she leaned her head on his shoulder. The other men around the pub looked on with jealousy as she planted her lips on his, her eyelids fluttering closed._

Their **joys**.

> _He embraced the woman whose life he was toying with, his smile not reaching his eyes even when she blushed an adorable shade of red. Without even a change of emotions, he led her into the hotel's bedroom. She slid open the glass doors, her expression coy as she pulled him to the balcony. He went along obediently, only smiling as she bent over the railings, her naked figure for all to see if the streets had not been devoid of life._

Their **reactions**.

> _The woman in ~~the same~~  a pretty green dress screamed when she saw his Mark. He pushed aside the pang of hurt he felt, telling himself to be in control of his feelings. Everything was simply a game. Don't get attached. He smiled his usual loving smile, patting her head as she struggled to free herself from the handcuffs. _
> 
> _"I find it pretty. Like a star in the night sky."_
> 
> _He caressed the right side of his face, his expression turning genuine as he pictured his Soulmark - his right eye only showing a white iris and pupil on a sea of black._
> 
> _"D-demon... Y-yo-you're mated to a d-demon!"_
> 
> _His expression flatlined as he stared into the green and blue eyes of the woman. She was handcuffed to the bed, her entrance slick and wet due to the foreplay just a minute ago._
> 
> _Before he had the chance to enter her, she had begged to see his Soulmark._
> 
> _He obeyed, thinking that she would find it as beautiful as he found it due to her love for stars._
> 
> _He **should've** known better. _

Their  **emotions**.

> _The same woman was on her knees, tears rolling down her cheeks and ruining the makeup she had painstakingly applied just thirty minutes ago. The kitchen floor was stained with her children's blood, their bodies scattered everywhere on the dining table. The man who she thought was always caring and tender to her was standing with a butcher knife in hand, his smile as gentle as the day he introduced himself into her life. All she felt was betrayal, righteous anger, and deep sadness._

Buuuuttttt~ That phase was over now - since he already grew bored of everyone in this town and didn't bother to expand his radius further. 

He sighed happily as he bit into the scones, his eyelids fluttering as he tasted the sweetness that was exactly to his liking. 

Now, he wasn't interested in starting a relationship with anyone but his Soulmate. And if he really did encounter the other half of his Soul... He would do his best to cherish and love them - whoever and whatever they are, regardless of gender or race or religion or whatever. 

And although he wanted to do his absolute best for them... He knew that he would grow bored if the loop continues.

That... that would kill the last piece of HoPe he has.

He closed his eyes, hiding his sadness behind the cup of espresso. 

* JUDGE

In his dark mindscape filled with an infinite amount of snow, he pressed the floating word.

*CHECK

Inner-him jabbed a thumb at himself.

* OPTION: ALL, HP, ATK, DEF, KARMIC RETRIBUTION, STATUS, SOUL 

He hesitated for a second before poking HP.

* CHESTER HP 1/1

... It decreased again, huh? 

He chuckled darkly under his breath, loathing that if he broke, his Soulmate would too. The disadvantage of having someone be bound to the Soul with you... was that if one dies, the other would follow. ~~Just like how he had died due to a knife wound, from shoulder to hip, that had mysteriously appeared many times over the course of this time loop(?).~~

The only reason why he had not lost all HoPe was due to his Soulmate. He had no right to off himself without his partner's consent. It wouldn't be fair to them to have their life ended so abruptly and not by old age. 

Even though he kept repeating that in his head... Humans were never meant to live in a never-ending cycle of isolation. They were social creatures in general, and with every relation he cut off, the deeper he falls into insanity (hopefully his Soulmate wouldn't mind having a broken partner). He opened his eyes but was only able to see with his left. The right side of his face was thickly covered by his fringe in order to avoid other humans pointing out how ~~beautiful~~ weird his Mark was.

He suspected that his Soulmate is... a Monster. 

If not, how would he be able to perform 'magic' and 'judgement'? 

Once again, he sighed for the nth time.

Not that he cared about their species, but if they were a canine or feline type Monster, he wouldn't be able to touch them no matter how much he felt for them. Having owned the two before as pets, he just felt it wrong to have intercourse with them - no matter if they walk on two legs or are sentient. 

His gloomy thoughts were interrupted when the chair opposite of him was moved and seated by a child. 

Well. This was different. Sometimes, even without his intervention, new things and people would pop up from time to time. So he simply shrugged the shock away.

His lone eye took in the child's appearance.

They were around maybe thirteen or fourteen of age, with short brown bob hair and slanted eyes - one brown and the other black. Their skin was on the yellow side, and they wore a striped blue and purple long sleeve shirt with jean shorts and cute blue rain boots. They were also carrying a flower pot with a buttercup in it settled on their lap, which he paid no mind to. 

"You lost, kiddo?"

The kid shook their head, a determined glint in their eyes as they scanned him up and down. He only raised a brow in return.

"Oh, you have company. That's new. Do you want to order anything, little one?"

Steve the waiter grinned as he walked over, nosy as per usual. This guy may look friendly, but he has a gossipy side that was worse than old ladies.

The kid pointed to something on the menu rather than replying, which made Steve's smile drop a little - probably because he wanted to pry whilst waiting. He hid his amused chuckles behind his cup of espresso, not wanting the two to notice his mirth. 

As soon as the waiter walked away, the kid shoved a hand forward.

"Jack. Nice to. Meet you."

Their voice was soft, shaky, and rough from disuse, making him strain his ears to hear them.

Whilst shaking their outstretched hand, his lips curved up into a polite smile, "A pleasure. You don't have to force yourself to speak, though, kid."

They shook their head hurriedly in denial - as if they needed to use their voice. 

"Hard to. Communicate. If write."

"I used to know a lot of people with selective mutism, kiddo. And judging by your body language and lack of vocal cord usage... You don't have to push yourself. I can understand ASL just fine."

The kid slumped their shoulders forward, their expression was full of relief. 

'Thank you.'

"No worries, doll."

They paused their conversation (if it could be called that) when the kid's (were they called Jack?) order came. A plate of pancakes and a cup of milk. Standard selection for young people. 

Only when Steve was out of hearing distance did they continue.

"So... Since you're not lost... did you simply desire to share a table with me? Not that I blame you for your excellent choice in company - I am quite the cool guy, after all."

They made a face, which he found absolutely hilarious. Many people would get turned off once he flipped his 'general amazingness with a side dish of obnoxiousity' switch on. This was his go-to attitude when he wanted someone to make an excuse and flee from him.

Should he continue teasing?

Before he could decide, however, the kid amazed him.

They **flirted back**.

'It's only normal to want to get the chance to know a cool guy such as yourself.'

With twin finger pistols and a wink at the end.

He raised a hand to cover his upturned lips, a little embarrassed that he was really smiling at the kid's behaviour. They were too adorable! 

"Judging by my dating guidebook..." He made a show of looking the kid up and down. "When one shows interest in another person, they would wear clothing that could be considered to have a lasting impact... Hmmm... Ironed... Neat... GASP! Could it be...? You must really want to impress me!"

When he cupped his cheeks as if trying to hide his blush, their expression turned weird again - it was as if they were having a hard time believing something.

'... You figured my intentions in a flash.'

He had to _hand_  (see what he did there? haha) it to the kid, they were doing a good job at bullshitting. Need to work more on their micro-expressions, though. 

"But of course! I am a master at reading people. It is fundamental, after all!"

With his chest puffed out, he made a show of raising his nose to the sky whilst grinning proudly.

'You're so cool. Are you made of beryllium, gold, and titanium? Cause you're _Be_ - _Au_ - _Ti_ -Full.'

... If he had not studied chemistry back then, that would've flown right over his head. This kid must be a nerd... a really smooth nerd. 

Damn, he really wanted to reply with 'chemistry pick up lines? now you're in my _element_!'. But since he needed to stay in character...

"Y-your suave rating is off the charts...! B-but! Don't think you've bested me just yet, kiddo. I am someone with **really** high standards."

'I can... cook spaghetti?'

Whilst they hesitated in signing the last bit, his eyes grew a little wider. How did this kid know his favourite lunchtime meal?

"I-impossible...! You've... Met my standards?!"

'Does that mean I get to date you now?'

He leaned forward so that his nose was only a few centimetres away from the kid, feeling amusement when their cheeks turned red.

"Kid... You know..."

They moved forward, their eyes flicking down to his lips before resuming their contact.

"Your flirting is really smooth that... I wish I can match your passion! But I'm sorry. I should not have encouraged you. That was not great of me. Maybe if you were eighteen, I wouldn't have minded. I know it will be hard for you to lose your intense desire for me, but I must ask that you try. Please don't wallow in self-pity because I won't go on a date with you! You're still cool! Just, uh, not at my level. THOUGH! Someday, you'll definitely find someone as great as me. Uh, maybe not. Nobody can be as great as me... guess you'll have to settle for second best..."

With that said, he leaned back and continued to sip the last of his remaining espresso, his expression relaxed as if he had not just almost kissed an underaged kid. The kid's eyes were wide open, and he could see a flash of disappointment in them. He knew that it wasn't because they were rejected. Nope. This kid wanted something from him - and it was important enough to not care if they had to date him for it.

The kid's body slumped back into their seat, almost dropping the flower pot due to their abrupt movements.

'Then, can we be friends, at least?'

He smiled mysteriously as he gently placed the empty cup down.

"I wonder?"

Without waiting for their reply, he placed a fifty-dollar note on the table before leaving without another word. It was only when he was at the door did he hear the kid trying to scramble after him. Before they could, however, he already jumped onto his bike and allowed his engine to purr. He rode off just as they left the cafe.

Later, kiddo! 

Suddenly... the world 'stuttered'. 

He was back inside the cafe, with 'Jack' sitting in front of him and Steve making his way over.

"Oh, you have company. That's new. Do you want to order anything, little one?"

What... Why and when did the 'starting point' change again?

Silently, he observed the kid whilst politely smiling at them like how he did just a few minutes ago - but inwardly, he was a mess. He disliked massive change. If he was not the cause of it, he preferred to stay far away from it. It had taken him about a couple of loops before he accepted Monsters. Now, this? This... was making him twitchy. 

The kid pointed at ~~pancakes~~ whatever was on the menu, and soon enough, they were alone. 

Unlike last time, the kid had immediately signed. This was another change without his involvement. His nerves spiked, causing him to release cold sweat. 

'Hello, mister! I'm Frisk. Do you mind if I accompany you for breakfast?'

What? Wasn't their name Jack?

His lips opened and closed, not knowing how to reply, before he cleared his throat.

_Stay calm. Don't stutter, Chester. You used to be a nationally wanted bank robber and 'cook'. Why should_ _you be afraid of change?! Isn't this a good sign?! Maybe the time loops will end soon!_ He clenched his fists under the table whilst scolding himself for being a wimp. 'Different' was supposed to be a positive indicator - so where did that mindset go? No, the question should be; when did he become so inflexible?

"Greetings, little one! I mind not your company since I know that you are simply unable to resist my greatness."

'Thank you, mister- sorry, I forgot to ask you for your name.'

Their words were calculated, and he knew they were acting as an innocent kid. He didn't know who put them up for this, but he wasn't going to allow them into his 'friend' list anytime soon. Not until he was sure that they were safe to interact with. And if anything, the world would 'reset', anyway. YOLO, right?

"Jack. You can call me the great and awesome Jack of all trades!"

_Spill all of your secrets to me, little one._

Chester grinned broadly at the little kid, his hair casting shadows over his eyes and obstructing the dangerous glint swirling within it. 

* * *

 

I picture Chester's eyes to look like this.

Whilst I picture Sans's "eyes" to look like this.

**Notes for the Chapter:**

> Thanks for reading this! It fills this writer with DETERMINATION!╰(▔∀▔)v


	2. Wolf in sheep's clothing

**Summary for the Chapter:**

> Stay innocent whilst being a BAMF!

When he woke up this time around, it was on his lovely paramour, the sofa, and not on his mischevious wife, the bed. He was wrapped snuggly in a blanket burrito, feeling immense relief at having not entered yet another cycle during his sleep.

Yesterday had been an absolute hell for him. He suspected that the kid, Frisk, has something to do with the time loopings.

The reason why he came to such a conclusion was all due to having experienced it first-hand. He saw how they had **controlled** time itself - bent it to their will. Whenever they failed to become 'friends' with him (he still didn't understand why), one way or another, he would end up having breakfast with them all over again. It was an **unending** cycle (he lost count after it exceeded a hundred), and he could only last so long before he became... _distracted_. So he gave them his number before he ~~fled~~ made a tactical retreat. 

Not one to admit defeat so easily, he reasoned that by interacting for a longer period of time with them, he may find clues as to how to stop these infernal loopings. No matter how fun it has been to live without caring for the consequences... he didn't want to be on his lonesome any longer. He **needed** companionship before he truly lost all his marbles. 

With an exhausted sigh, he covered his eyes with his forearms, not wanting to be reminded of how empty his ~~mansion~~ house was. With his eyes closed and his ears opened, he managed to create a perfect illusion of having people here with him by listening to the TV and radio sounds.

The world, on the other hand, just despised him. Or maybe that was his phone. Why didn't he put it in silent mode again?

_~you've always been a piece of shit! if I could kill you, I would. But it's frown upon in all fifty states. Having said that... BURN. IN. HEL-_

"Hello. This is a recording. Please leave your message after pressing the red button, thank you."

As soon as he said that in his most fanciful British accent, he hung up and placed his phone in silent mode. Not even caring that it had started to soundlessly ring again, he threw it wherever and snuggled back into his blanket burrito, leaving only his platinum bleached hair with one streak of blue poking out.

Speaking of hair... He was getting bored of this colour. Should he dye it purple?

He sighed, "... What's the point? It'll all reset, anyway." 

Seeing that he won't be getting any more sleep anytime soon, he unwrapped from the blanket burrito and stretched, groaning in satisfaction when his spine popped in several places.  

Always one to prioritise his hygiene, he took a quick shower before making his way to the kitchen, having randomly grabbed a pair of shirt and pants from his bathroom walk-in closet.

Time for some grub. 

But what should he do afterwards, though? Go grocery shopping? Drive randomly around? Continue with his side projects? Attend advanced flower arrangement classes? Learn yet another language? Buy a turtle for a pet? Pull a couple of pranks? Hack the Mayor's database? Visit the zoo? 

Ahh, so many things to do... And too much time to have.

Whilst he pondered, he zombie shuffled into the kitchen and reached for the first thing he laid eyes upon. Seeing that it was a bag of tortilla chips, his brain suddenly remembered a funny joke he had heard from a couple of drunks a few resets ago.

So as he poured the chips into a bowl, he giggled to himself.

"How do you get a baby into a smol bowl? With a blender. How do you get it out? With tortilla chips!"

As soon as he said the last word, he burst out into cackles, having to wipe the tears of mirth leaking from his eyes. 

Oh, man. He needed to find those drunks again. Their brand of humour was to die for. 

"ՇђคՇ'ร ђ๏ггєภ๔๏ยร."

An unfamiliar and static-like voice caused him to whirl around with his handgun ready (thank goodness he had armed his mansion during the final 15th September reset), his eyes roaming in search for trespassers. When he didn't see anything amiss, he didn't do something foolish like relaxing his stance or letting his guard down. Nope. He carefully stalked through the kitchen with his gun's safety off, cautiously reaching for another handgun taped underneath the kitchen bar. When he finished three laps around the kitchen and found that there truly was nobody, he made his way out.

It was now instinctual for him to secure the parameter at the slightest of unease and be on constant vigilance after what had happened during loop 4444, cycle 17 - which he, to be quite frank, wanted to forget.

Every potential hiding place was carefully examined. Every nook and cranny. Yet there was still nobody but him in this whole four-story mansion. Even the underground levels and CCTV footages were examined. End result? His home has not been breached. 

Had those words all been in his head? Was he loosing what was left of his mind?

He shuddered at the alarming thought.

What was the difference between an animal and him?

Intelligence.

If he were to fall into true insanity, he would end up an instinct-driven beast - and with all of the dangerous skills he had accumulated throughout the time loopings? That would make him a danger to the city (nation, too, if he were honest). And that would be a terrible idea. Because... When the police deem someone a national threat, they would activate Manhunt Protocol 2.0.

Which was to track down the criminal's Soulmate and  **get rid** of them. So unless his Mate was a BAMF with teleportation skillz, he can't risk breaching that protocol.

He saw it happen many times. Soulmates of terrorists getting gunned down without a clue why they were targeted - how they were even found was still a mystery to him. Hell, it had even happened to him once. When his internet hacking heists had caused a major economic crisis. Although they never did find out who his Soulmate was, it had frightened him enough to stop his habit of e-stealing money from the banks.

The feds had been desperate to catch him, even searching for people with golden eyes. Afraid that he would compromise his Soulmate's safety, he hid behind contact lenses, eyepatches, and sunglasses - constantly changing them and not stepping a foot out of the house if not needed. Whatever can go wrong, will go wrong. Hell, he even made sure to wipe clean the vehicles he used and wear gloves so that his prints were never discovered. That was how paranoid he was. 

But, well, that was all in the past now. He wasn't on anyone's radar in this cycle (apart from Frisk's, apparently). 

When he returned to the kitchen, his guard was instantly doubled (if that was even possible at this point). The few tortilla chips that had fallen to the floor had been cleared, and there was even his favourite condiment bottle next to the bowl, along with a glass of milk.

Because of the bodyguard and mercenary training he did many loops ago, he surveyed the whole kitchen AGAIN, his paranoia spiking to insane levels. When nobody was found, he flipped on the safety of his handguns but continued to hold it at a ready. As he got nearer to the bowl, however, he felt that the temperature was gradually dropping. He shivered, his thumbs already hovering over the safety switches. 

As soon as he loomed over the bowl of chips, however, the cold left unexpectedly as it came. He gave one last wary look around the kitchen, before tucking a handgun in his pants and finally grabbing the three items with his free hand. He moved to the living room, sitting stiffly on the sofa as he stared at the TV. 

He was too jumpy to truly release his hold on a gun, so he ate with one hand, his eyes not really focused on the screen since they were too busy with their wandering. 

As the day progresses without anything happening (apart from the constant silent screaming of his cell), he completely relaxed, having already taped one handgun back underneath the kitchen bar, whilst the other one was still within easy reach.

Now he was simply bored. The advanced ikebana class was in the early morning, but due to his paranoia, didn't attend. At least that was one less option to choose from, right? Gotta think positive. 

With a grumpy mumble, he exhaled loudly before he stood up and grabbed the first jacket he saw on his way over to the front door. It was a nice green bomber parka with a fur-lined hood. He donned it over his plain white tee whilst also toeing his favourite pair of fluffy blue slippers on. 

The ten-minute walk from his front door to the garage has always been something he hated. Why did he tell the construction workers to build them so far apart from each other, again? 

When he finally arrived at his garage, he pushed in the code and let it scan his retina. He really needed to change the access locks. It was time-consuming. Not to mention it screams 'something suspicious is in here!'. 

The first thing he saw when the garage (which could fit about twenty semi trucks) doors flip open was a missile warhead. He couldn't help but facepalm. 

"I should really cover that..."

He quickly entered, the overhead lights turned on automatically as he continued further inside. He stopped in front of a wardrobe and took out a few sheets, not minding the different colours. After spending a few minutes covering the more dangerous things in his garage, he made his way towards his baby - the 'gangsta' chopper. 

He pulled on a pair of leather gloves before he hopped onto his baby and started her up, loving the sound she made. He then donned on his loving predator wolf helmet that he painted to look like a wolf's skull. The minute he zoomed out of the garage, the overhead lights turned off and the garage doors have begun to close. 

The drive cleared his mind as he sped through the roads, not minding that some had cursed him as he passed by their turtle slow vehicles. He laughed and flipped them off, all the whilst grinning like a madman. He even had the James Bond theme song playing in his helmet speaker. Classic. 

"Tutututu dududung tutututu dududung~ Ting ting~ Dun dun dun~"

It was only after a few hours of aimlessly driving around did he notice that he was almost out of gas. He rolled his eyes upwards as he pulled up the GPS in his head to lead him to the nearest gas station. 

The second he stopped at one pump, he was greeted with an eyebrow-raising sight.

There was a black limo, a really long one, just next to his pump. That wasn't what surprised him. Nope. It was the people inside. Or perhaps he should say Monsters rather than people. 

The driver, or who he assumed as the driver, was pumping oil into the tank whilst looking nervous as heck. 

He rolled his eyes at the dude before jumping off his chopper and filling her up. Whilst he did so, his eyes - which was hidden behind his helmet - habitually roamed the surroundings, his eyebrows furrowing with every little thing he noticed. 

There were armed guards everywhere, dressed in military attire, standing near the limo and around the patrol station. Some were also inside their vehicles, as if ready to give chase at any time in case of anything. This wasn't all too alarming because Monsters were still new on the surface and they needed to be guarded at all times whilst they deal with the political leaders. But what truly raised his hackles was the snipers on the roof just beside the station. His helmet came with electronic binoculars functions, so it was obvious to him that these snipers were not part of the armed guards' team.

One, they weren't wearing the same military uniforms.

Two, their comms didn't look military. It was more amateurish. 

Three, their postures were off, as if they didn't really know how to position themselves whilst aiming.

Four, their rifle handling was painful to look at.

There were many reasons, but most of all... Their expression of fear and hatred was obvious.

He chose to ignore this all. It didn't concern him.

And although he had decided to do just that, his brain did take into account of all the hostiles' position, as well as the safest escape route. Being the jack of all trades truly came in handy at times like this. 

Soon enough, he paid for his baby's gas and drove off in a hurry, not wanting to get involved in the assassination. Human.. or in this case, Monster, life wasn't important to him. He lived too long to give a shite about that. Lives come and go. Natural order. Some die of old age, some from accidents. He learnt that the hard way. The future may be unpredictable to all, but to him...?

He had enough of playing hero.

He wasn't that far when he heard an explosion from behind of him. His heart thudded with grief at the losses, but he pushed these unnecessary feelings aside. 

_Don't get involved, Chester._

_Don't bring more pain to yourself._

As his heart calmed and his face turned emotionless, he pulled to the side and took off his helmet. When he turned his head behind, he saw black smoke coming from the gas station.

Then, he felt the familiar sensation of the world stuttering.

He was back again at the gas station, pumping his baby with oil. He leaned his spine against the fuel dispenser as he closed his eyes in resignation.

His playlist halted in favour of his cell ringing. He grimaced. He had expected it but was still in somewhat denial. This just proved to him that denial wasn't going to change things. Just like how ignoring problems won't make them go away.

Whilst he tapped the side of his helmet, where his right ear was, he stared at the limo. A brown-haired child was sitting amongst a group of Monsters, their hands trembling as they held their phone to their ear, their tight grip causing their knuckles to turn white. 

"Hello. This is a recor-"

He was cut off by the child's shaky voice.

"P-please. D-d-don't ha-hang up."

"... Frisk. Sorry, kiddo. But I'm a little busy here."

He made sure to sound apologetic whilst internally shouting a mantra to himself. Don't get involved. Don't get involved. **Don't** get involved! 

"I need. Y-your help. Please. Jack."

He grimaced. He knew that they were forcing themselves to talk. He pitied the child, but he was also furious at them. 

They caused the time loopings, yet they expect him to help them? After making him jaded like this? After having caused him to lose faith in humanity? After having made him disregard human life? After all that? Just like that?

When he was silent for too long, Frisk's breath hitched higher. He saw the group of Monsters looking at the child with confusion and worry.

"P-please."

He closed his eyes, a frown on his face. His mind was in a state of disarray.

He needed to help them. They were the only clue he had about the time loopings, and if they continued to die here... He knew they would simply turn time back to yesterday. 

But he didn't want to help them!

"Please. My family. In trouble. Please. J-jack."

After a minute of thinking, he sighed out loud.

He did tell himself that he would change, didn't he? 

Helping someone wasn't something he did. So he should start off with that.

"Heh. Alright! I, the great Jack, has got your back. What do you need me to do?"

He saw their shoulders sag into relief as they let loose a shaky breath. He also heard a few murmurs of confusion on their end of the line. 

"Where are. You? Can you. Come?"

"I'm already here, kiddo." They blinked rapidly at that, their expression hilarious to look at. "To your left."

He waved at them when they turned to look out the window. This time, he did laugh when their mouth was left open in disbelief. The others in the limo were looking at him too, but he ignored them in favour of paying for the gas.

"W-why? How?"

"As the same as every good driver, I needa fill this baby up. Now then, are you perhaps wanting the help of someone as great as I to get rid of those snipers?"

They didn't reply him, only pushing the car door open and rushing to him, the phone forgotten on the seat.

"M-my child!"

A goat Monster in an elegant purple dress rushed to follow, along with some of the other Monsters and the military guards.

'Jack! How did you know about them?'

Frisk signed immediately after stopping in front of him, their expression frantic. He, on the other hand, calmly ended their call and went down on one knee so that they were both on eye level. 

"I am the master of all trades, kiddo." He made sure to make his voice playful so that they knew he was winking inside his helmet. "The awesome me has dabbled in many things! Especially my observation skills! That one I have mastered beyond anything imaginable! And my my. I had no idea that you are THE Frisk. The Monsters' official ambassador."

The Monsters and military dudes were immediately wary as soon as those words left his lips. 

'I am sorry I didn't tell you. Will you still help me, regardless of my identity?'

"No worries, doll. Someone as great as you can only have friends that are equally as great. Tell your guards to not shoot me and I'll deal with... the issue at hand. I'll also need you to hire me as a mercenary or a bodyguard for this. Only then will I be legally allowed to defend you without complications. We can discuss the price afterwards."

The kid nodded before they turned to the other goat Monster with a crown in between those cool as fuck horns and purple cape covering his entire body. Their eyes were filled with determination. 

'Please inform the security to not hurt him, dad. Jack's my bodyguard.'

The goat frowned, whilst a fish Monster beside of him crossed her arms, looking at Chester with suspicion. Her long red hair was in a ponytail, and she wore a metallic armor for protection. He wondered idly if she has a spare eyepatch he could lend. He couldn't really remove his helmet because he didn't bring his. And showing others his Soulmark was not something he wanted. 

"Frisk..."

'Please, dad! Trust me.'

"... Very well. Major, please refrain your men from attacking this gentleman over here. He is, apparently, my child's bodyguard."

Before the major had any time to respond, Chester has already pushed Frisk into the nearest Monster near them - which was a skeleton in a hoodie. He didn't have time to blink in awe at a walking skeleton, too busy looking at the roof.

The spot Frisk had been standing on had a bullet hole in it, which in turn, caused everybody to up their guards as the fish Monster ushered the two goat Monsters into the limo whilst the skeleton was doing the same to Frisk.

The military dudes were all running around whilst the major shouted orders.

Chester frowned as he pulled out his revolvers. He wished he had packed a rifle or something.

Without any hesitation, he fired the second shot of the day, causing many military personals to aim their assault rifles at him. He paid them half a mind as he brought up both his two revolvers to aim the rooftops and continued to shoot, running forwards to the building whilst also dodging some bullets here and there.

The snipers were in a panic as they frantically shot at Chester, ignoring everyone else but their sole shooter. An elementary mistake he had once made too.

He lured their scopes away from the flammable fuel dispensers whilst simultaneously coming closer to the building they were on. They were seriously a bad shot.

Having been near a truck, he hid behind it as he reloaded. The snipers didn't even count their shots like he did nor did they coordinate with each other. It was laughable.

When he counted the last of their bullets, he rushed out from the truck and turned his inbuilt binoculars online.

Six bullets were released from his handguns, three from each.

Five headshots and one non-lethal body shot confirmed.

These noobs truly were laughable. The first thing when being a sniper... Choose a more proper location. Who in their right minds would shoot at such a short distance? Especially when their targets were surrounded by military professionals. Get out of firing range for fuck's sake! 

He released a breath of air as he tucked his guns back into their holsters underneath his parka.

When he turned back to tell the major to get one of his men to secure the guy for information, his whole body froze as his eyes landed on his chopper. 

He almost screamed bloody murder at the sight of his beautiful baby covered in bullet holes!

"Nooooooooo!!! My baby!!! My precious baby!!!"

He cried out as he pushed the military dudes away and hugged his poor chopper.

**Notes for the Chapter:**

> Thank you for your support and positive comments! It fills this writer with DETERMINATION!╰(▔∀▔)╯

**Author's Note:**

> If you like my stories and would like to show your support, please consider buying me [coffee ](https://ko-fi.com/V7V5HKR7)@ https://ko-fi.com/V7V5HKR7 ! It'll be heavily appreciated! (๑•̀ㅁ•́ฅ


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